Acetylsalicylsalicylic acid: a potentially immunogenic impurity in acetylsalicylic acid

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Abstract
A study has been made of the chemical reactivity of a commonly occurring impurity in commercial acetylsalicylic acid preparations, acetylsalicylsalicylic acid. This impurity in aqueous solutions of pH 7·4-10·2 at 37° reacts with amines to produce salicylamide derivatives. The reaction rates are proportional to the concentration of amine in its free base form. Since the rates are appreciable even at physiological pH and the N-salicyloyl group has been reported to be an antigenic determinant in acetylsalicylic acid allergy, it is suggested that acetylsalicylsalicylic acid must be considered as a potentially immunogenic substance being involved in the development of allergic reactions to acetylsalicylic acid preparations.

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